反应详情

To a clean, dry 100 mL round bottom flask is added methyl 3-hydroxy-5-nitrobenzoate (240a, 0.4 g, 2 mmole, 1 eq), orthofluorobenzyl bromide (0.57 g, 3 mmole, 1.5 eq), potassium carbonate (0.56 g, 4 mmole, 2 eq), and DMF (3 mL). The reaction mixture was stirred at room temperature for 18 h and quenched with water and ethyl acetate. The product was extracted into the organic layer, dried over magnesium sulfate, filtered and evaporated. A white solid was obtained (0.49 g, 80% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.41 (s, 1H), 8.09 (s, 1H), 8.00 (s, 1H), 7.59 (dt, 1H, J=1.8, 8.0 Hz), 7.42 (m, 1H), 7.24 (dt, 1H, J=1.0, 8.0 Hz), 7.22 (dt, 1H, J=1.3, 8.0 Hz), 5.33 (s, 2H), 3.98 (s, 3H). Calc'd for C15H12FNO5; m/z (M+H+)=306; found 306.

1. customTo a clean, dry 100 mL round bottom flask
2. customquenched with water and ethyl acetate
3. extractionThe product was extracted into the organic layer
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. customevaporated
7. customA white solid was obtained (0.49 g, 80% yield)